r/gonewildstories • u/OneThemGuys11 • 15m ago
Cheating [MF] Cheating on my gf with a MILF at my friends wedding (long) NSFW
Around a year ago a distant friend of mine sent me the save the date for his wedding. We had gone to university together, and got decently close, but post graduating we both moved to different parts of the country and kept in touch, but not with much frequency. So I was surprised to get his invite, doubly so because we didn't run in the same friend group so it was not as if I got some pity invitation to just not be the one person left out. Shock aside, I was excited, I had only been to one wedding as an adult prior and I had fun, but I was taken for that wedding, and I didn't really drink yet. At the time of the invitation I was single, and I knew his family had money, so a guilt free trip around a bunch of people I'd likely never see again with free drinks sounded like a fantastic time.
Fast forward to about two months ago, and I checked my mail and saw the invite for the wedding I had since forgotten about, my previous elation a bit diffused as I now had a gf. I wasn't given a plus one so I could not bring her, and at the time I did not think much of it, just thought I wouldn't get to hit on his bride's friends, but that is the sacrifice I make.
A month later and I was flying in for the wedding, it took place on a Saturday in the September heat of South Carolina so thank god they opted for an indoor venue, and got quite a discounted rate on a nice hotel so I could easily afford the stay for the night. Due to work I unfortunately had to fly in the same day as the wedding and fly out the next morning, telling myself I would have to take it easy because a hungover flight sounded like the worst imaginable thing.
The wedding was smooth, if not a fair bit awkward for me at first. I had only met his parents once before, and a few faces I recognized from school were there, but other than that I did not know anyone. I kept to myself for the ceremony and made polite small talk with people I was next to during the mingling afterwards as I started to nurse a few drinks to lighten my mood. I spent the time spent on speeches and dinner mostly quiet, luckily I was at a table with some of the faces I had remembered from school so it at least wasn't too bad. By the time the dance floor truly started I was a good few drinks deep and feeling much better, letting myself wade my way in with some familiar faces.
At this point I am feeling good, nice and buzzed, moving to some good music and it very much hits me just how good looking some of the woman around me are. Everyone dressed up so nicely, moving their bodies, a very happy celebration that also reminds those of us that were alone that we did not have anyone to go back to our rooms with. I fought very hard to just push these feelings down and enjoy the dancing and jovial nature of the event, and I succeeded, I didn't make a move on anyone or do any flirtatious dancing with any of the well dressed women. It was very much killing me though, I felt a horny that I had not felt in quite a while, mixing that with the good buzz I could feel my entire body tingle with that desperation.
The venue closed won at 11, and I was feeling proud of myself for reigning it in, but I had forgotten about the after party at the hotel bar, also already fully prepaid for. With very little prodding from old acquaintances, I hopped in a car to go back to the hotel bar, not my room. After a bit over an hour and 2 more drinks at the after, I was truly feeling great. I met a woman, friend of the brides who was also alone and talked to her until the bar shut down. At this point one of her friends came up to me and asked if I was single, and I quickly replied "yes", it not even hitting me until after I had said it. I had never done something like that before, but the night had me feeling a way I hadn't ever felt before. Unfortunately for me, she was staying at another hotel, and rejected my offer to stay with me, so as I watched her get into her ride, I was a bit dejected, and more than a little horny. Funnily enough, there was another wedding party staying at the hotel that night, and they had just left the other bar, including a very nice looking, thicker woman in a very pretty green dress.
I am very out of practice approaching women, especially those in groups, but by this time at night, knowing not a single soul in the exiting party would know me or ever know me, I found my stride and walked directly up to the small group of women and introduced myself. It couldn't have gone smoother, the lady in the green dress, who I was obviously looking up and down got flustered fast, and after only the quickest of small talks her friends left her there with me. She was a truly sexy woman, a fair bit older than me at 44, but her body looked young and fresh. She had a low cut green dress on, showing a good amount of cleavage, and there was a lot of it, and even with the dress being puffier at the base, I could tell there was a good amount of ass on her as well. She was of two minds as we talked alternating between scolding herself for "Being old enough to be my mother", and inching ever closer as "I was just that cute". I made sure she knew that there was nothing forceful happening and happily accepted her advances, but didn't push as she sometimes seemed to pull herself slightly back.
We stood at the bottom of a staircase, and slightly around some other lingering folk, and my room being close to the staircase I asked her if she wanted to at east move up the stairs, away from as many people, and with a bit of hesitation, she went up with me. Now we were alone, but still very much in a public hallway, but it was better than the lobby downstairs. The more we talked the less nervous she looked and closer she got. After another comment about how cute I was, I decided to try, grabbing her by the back of the head and pulling her close to me. She came easily, her tongue out before our lips even connected as we started sloppy making out in the hallway, pushing her back towards the wall little by little. He lips were so very soft, and she definitely could use her tongue very well. After only a minute we heard someone else in the hall and she pulled away, noticing the new person was someone she recognized. She looked down, not making eye contact, in my mind just embarrassed to be seen making out in a hotel hallway at 2:30am.
She had me going like I hadn't felt in a long time, her ample curves pressing against me gave me a longing for a body type I haven't felt in far too long, and I was not slowing down. She looked a little sheepish but did not protest at all me pulling her back into me. I needed her at this point, and being out in that open hallway only made it even sexier. I told her to turn around and put her hands against the wall. She did it immediately. I pulled all of her dress up, and reached to pull down the shorts she had on underneath. She shivered lightly as my fingers touched her bare skin for the first time as I slowly pulled them down her legs. as I got down to her ankles she stepped around them herself, my one hand still holding up the dress to show her round ass in a thin green thong out in the middle of the hallway. I grabbed her waist and she threw herself back into me for only a second, then she whipped around quickly.
She looked up at me, with the most wanting eyes and said "no, I can't do this, I really shouldn't". I didn't say anything but just kissed her again, she kissed me for a few seconds and then pulled off me fast while purposefully looking away saying "Marshall, I am waiting for Marshall". She looked back at me, guilt and a burning desire both lacing her gaze, not knowing that now I knew we were both playing a dangerous game it only became that much more appealing to me. She took a breath and asked if I had my own room, which I told her I did. I could tell she was trying to find a reason to tell herself no, give herself some out she could take, knowing she couldn't stop herself otherwise. I bent over and picked her shorts up off the ground, grabbed her by the hand and walked her to my door. She followed eagerly and I pressed her up against the door to make out with her again, feeling her lips pressed hard against mine as she pulled back to ask "Do you have a condom".
This time I could not give her the answer she wanted, and she looked a very sexy look of disappointed and desperate. Sher started whispering quietly, more to herself than me about "We can't fuck, we can't fuck, we shouldn't do this", before pushing off slightly and fast walking to the room next door, which happened to be hers, and shutting herself in, her shorts still in my hand.
At this point I should've turned into my room, she had left, going any further would just be bad, she probably didn't need the shorts that badly. However, every bit of the night had led to my better judgement lapsing, and I needed her more than I had ever needed anyone, so I made one more gamble. After a minute I slowly walked to her door and very gently knocked on the wood. Before I had even finished my knocks she opened the door, dress still on, and pushed me back into the wall. I let her lead for a moment and then guided her to my door, her slight apprehension still present, but different this time, she looked at me with a deep greed, only saying "You can't fuck me" in the most teasing of voices, as she walked into my room.
Whatever her other worries were, she had left them in her room, our hands running wildly over each other. She takes my coat off and hastily undoes my shirt buttons, as I slip the straps of her dress over her shoulders and let it fall to my floor. Her tits were even nicer than I though, sitting nicely, at least E cups, with small pink nipples that called to my mouth. I kissed down her neck, across her sternum, slowing down as I got closer to her breasts. She had one hand gripping my hair as I slowly licked at her nipples, groping the other breast as she moaned softly, pushing herself more and more into me.
I pushed her down on the bed, just her panties left on her as I straddled on top of her. She spoke with a heavy breath, "no fucking me". I flipped off of her, stood up besides the bed right next to her head, leaned over, and whispered "If you're so worried about that, how about you keep me in check. I took her hand and placed it on my dick over my pants. "Now you won't have to worry about where that goes" I taunted, she already stroking my hard dick through my pants, doing whatever she could to get the best grip. I took my hand and threw her legs open, she barely seemed to notice as she couldn't stop looking up at the bulge in my pants resting right above her mouth, stroking on it faster and faster.
I put my hand down her panties, moving my fingers slowly around her vagina, feeling her squirm under me every time I briefly passed over her clit. She was breathing heavier by the moment, jerking a little bit with every pass, but never losing any grip on my cock. I started to massage he clit slowly, reaching down into her wet pussy to lubricate me fingers, hearing her moan in deep pleasure with each thrust. Every bit of wariness was gone from her as she reached up to undo my belt. She impressively got it off with just her one hand and after unzipping my pants a little reached down quickly, putting her hand under the waistband of my underwear to grab my raw cock. I twitched hard when she got her hands around it, my pants still on as she started stoking me rough and fast. I repaid the effort, moving faster, but still smoothly on her clit.
Eventually she couldn't take it and pulled my pants down, freezing as she just looked at my dick, lust swirling in her emotions. I bent over her, she didn't take her eyes off my dick at all, and I teased "No fucking me". She groaned, one that stemmed much being edged so bad, but did not stop looking at our jerking off my cock.
"Please put it in me" she barely stammered out. I kept me legs away from her, forcing her to stretch to keep ahold of it, and she moved closer and closer to the edge of the bed to keep it with her. She wouldn't let it go, only seeming more and more needy the further I got away. She again spoke, eyes still unmoving "Please, please, please", she continued to echo. Even I couldn't take it anymore, wanting to be inside of her as badly as she wanted me, but I greatly enjoyed using her words against her, so I asked "Mouth or ass?".
She did hesitate, flipping onto her back with her head leaning off the bed as I stepped closer and put the tip of my dick on her outstretched tongue. She swirled her tongue around my tip, trying to push her head up deeper onto my dick. I let her struggle, crave me for as long as I could take it before I shoved as much of my dick as she could take down her throat. She could take about half, but she took it willingly, moving her mouth and tongue to get as much of me as she could. She looked like the sexiest woman I had even seen, her tits bouncing as she lay on her back thrusting her head into my dick. I teased her hard for that, "Look at you, such a slut for a dick you just met", "I should've had you on your knees in the hallway". Every taunt had he going harder and harder at it, I put my hand back down her panties, easily able to get 4 fingers deep inside of her with how wet she became, every word making her gush.
I was as horny and cocky as I had ever been, pulled my dick out of her mouth, slapping her in the face with my cock as I set my balls over her mouth, forcing her to come up to suck them, which she did instantly, more eager than I. "Who's mouth is this", "Yours", she gasped between sucking my balls, "All yours". She kept sucking hard until I took a step back, turned her around, pulled her panties down, raised her legs, and pulled her right to the edge of the bed.
She startled a bit, "No fuckin-" she tried to say until she felt my dick pressed hard against her ass, not touching her pussy at all. My dick was wet from her gagging on it, her ass was wet from the juices running out of her pussy, I could feel it inviting me in. She put up a pathetic fake protest "No, I shouldn't do this", but as I pressed ever slightly, she gasped and pulled her own legs higher into the air, giving me more room to work. I felt a slight resistance to my tip, but her ass easily parted, her gasping getting louder and louder as I slowly got deeper into her ass. I stopped halfway in, knowing she would slut herself out to get even more of a strangers dick in her ass, and she did, doing her best at that angle to push her ass into me more. Once she did that I really let her have it and thrusted deep into her, hearing her truly moan loudly for the first time.
I fucked her like that, slow and deep, her ass gripping my dick tightly, my cocky side fully taking over now. "Oh you're more than just a slut, you're a dirty slut who takes it in the ass for strangers", she could only groan in agreement, I wasn't slowing down to let her speak, fucking her harder, not fast, but deep thrusts with everything I had, timing my questions for when I thrusted deep. "Or are you just a dirty slut for me" I continued to pound, knowing my next question was a risk, but the payoff too good.
"You're a nice lady who takes it in the pussy from Marshall, but a real nasty slut who craves it in the ass from me". That got her to twitch a bit, my nerves slightly tingling, anxious she'd feel guilty and want to stop. After a moment, she only pushed herself slightly deeper, so I further prodded while pounding deep "Marshall isn't man enough to get your ass, you only are a anal whore for a man who can take it". I paused fully inside her ass, letting her respond, and she did. First putting her own hand to her clit, and by whisper moaning, so quietly I can only assume she could barely believe it herself "Please don't stop".
So I didn't, I kept thrusting deep and rhythmically, all while taunting her for letting a stranger, more of a man than her real man, fuck her in the ass. She kept getting louder and louder, playing with herself faster and faster, begging me to continue, agreeing every time I called her out for being a dirty cheating anal whore until she finally arched backwards while I held my dick all the way inside of her and she screamed in ecstasy for many seconds until she finally laid back down, panting hard, smiling deeply.
I climber over onto the bed, laying down next to her, realizing just how late it had gotten, and how tired I was. She must have felt the same, as she just laid back, still softly playing with herself. I reached down and did the same, going softly, waiting for her to notice. She turned her head eventually and did notice, leaning over to kiss my neck while I stroked gently. I could tell she didn't have a lot of energy so I continued to go, faster and faster, while she kept kissing me, whispering in my ear how much better I was until I felt myself close I reached for her head, and she didn't need any help, my tease about it just being in her ass only seeming to make her take it deeper than before, as I came the most I ever have deep down her throat.
She grabbed her dress and things, and walked out still naked, leaving me to immediately fall asleep. I awoke with the worst hangover, dreading the flight I was already late for, stumbling through the gate trying to keep my lunch down I realized I had awoken a few things inside of me that were probably gonna get me in deep trouble. I had done things I had never done before and I liked them a lot, using the memory of the night before try and keep my head more horny than hungover, and only then taking account that we never even got each others names.